The closer Matt Nathanson gets to the Pacific Ocean, the more the memories start flooding back.

"In San Francisco, as you get to the 40s" -- the avenues, he means -- "it becomes foggy and moody and beautiful and romantic and sad," he said. "It really pulls a lot of stuff out of me."

There are memories of falling in and out of love under the Golden Gate Bridge; of wasting summer afternoons in a basement in Berkeley; of breaking someone's heart on the beach on the Fourth of July.

It is these experiences that color Nathanson's latest record, his most site specific -- and by extension, most personal -- to date.

"This is the first time I've taken actual data points from my life and not sanded off the specifics," Nathanson said of "The Last of the Great Pretenders" (Vanguard), his eighth studio album. "It's the first time where the descriptions are based on places where I live and been and people I know."

For Nathanson, who performs at Alive@Five in Stamford on Thursday, Aug. 1, the fresh direction came from the realization that "I was shading parts of myself that I didn't think people wanted to hear."

For one, he was hesitant to bring up San Francisco. When the streets names and places started popping up in his lyrics, it made him feel self-conscious.

"I thought, `Is this record really about San Fransisco?,' " recalled Nathanson, who has lived in the city for the past 20 years. "But part of the plan was that I didn't want to pull any punches; I didn't want to assassinate any creative ideas."

Neither did he want to assassinate any of his past mistakes. Songs like "Come On Get Higher" -- the singer's platinum-selling 2008 single -- paints Nathanson as a winsome, lovelorn troubadour. But that characterization, he said, obscures the darker side of his personality.

"I said to myself, `If I'm writing songs for a living, they deserve all of my unique, broken parts,' " he said.

Those "broken parts" are revealed, warts and all, on songs like "Earthquake Weather." "I'd kill anyone who'd treat you as bad as I do," Nathanson sings, before adding, "It comes natural to be so cruel, to be an a----- to someone as good as you."

Sonically, the album is playful and spontaneous -- a sign that Nathanson applied the same unmitigated approach to his compositions as he did to his lyrics. Recording the LP at Decibelle, a small, in-home studio in San Fransico's Noe Valley neighborhood (a 10 minute bike ride from his home), Nathanson "aimed not to impart my external ideas on all the songs."

"There was a sense that I wanted to stay out of the way of what was going on," said the singer, who recorded the album with a cadre of musician friends. "In the past, I alpha maled my way in. But this felt like a team, a unit of people.

"Sonically," he added, "It feels more honest."

During the making of "Last of the Great Pretenders," Nathanson was inspired by "all the great storytellers" -- Raymond Carter, Bob Dylan -- who "brought the reader or the listener in and set a scene with all these vivid details.

"I wanted so badly to leave some of that in my songs," he said.

Nathanson does just that on his latest album, taking listeners on a meditative stroll to the Pacific Ocean and, in the process, revealing things about himself that we, as listeners, never knew -- his love for his city, his memories, his mistakes.